Things to do in Pittsfield
183 places, local favorites first.
Sort: Local favorites · A to Z
Herman Melville's Arrowhead
Landmark and historical building · 780 Holmes Rd
Berkshire Peak Apartments
Landmark and historical building · 341 West St
Samuel Harrison House
Landmark and historical building · 82 Third St
Pittsfield Shakespeare In The Park
Theaters and performance venues · 74 1st St
On the map
Where these 183 places are in Pittsfield.
Talk & tips
Favorites, openings and closings from Pittsfield neighbors.
Weigh in
Is Rj's Restaurant Seafood/chops/pasta the best place to eat in Pittsfield?
Your answer becomes a post in Town Square.
Share a tip
Some place details from Overture Maps (CDLA-Permissive-2.0), checked against the Census town line. Places added by neighbors go live once a second neighbor confirms them. Spot a mistake? Open the place and tap Edit mode.
How we sort and count
Each list puts neighbor favorites first (ratings and photos), then the most complete listings (a website, a phone number, a note), with local, independent spots ahead of national chains. Categories come from each place’s map category, so a café filed under “Shops” still shows up with the cafés. “A five-minute walk” is a quarter mile from the busiest spot on the map. Per-1,000 figures use the Census population.